Medroxyprogesterone Acetate

Liam

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General information

external image 512px-Medroxyprogesterone_acetate.svg.pngexternal image 756px-17-acetato_de_medroxiprogesterona3D.png
IUPAC Name
[(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-
2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
Molar mass
386.52 g/mol
Formula
C24H34O4
Melting point
208°C
Boiling point
496°C, decomposes
Density
1.1 g/cm³

Element
C
H
O
Mass composition
74.6%
8.8%
16.6%
Molar composition
38.7%
54.8%
6.5%

History

MPA was independently discovered in 1956 by Syntex and the Upjohn Company. It was first introduced on 18 June 1959 by Upjohn in the United States under the brand name Provera (2.5, 5, and 10 mg tablets) for the treatment of amenorrhea, metrorrhagia, and recurrent miscarriage. An intramuscular formulation, Depo-Provera (400 mg/mL MPA), was also introduced in 1960 in the U.S. for the treatment of endometrial and renal cancer.

Production

Medroxyprogesterone acetate is produced via the esterification of medroxyprogesterone, or via the methylation of hydroxyprogesterone acetate.

Availability

Medroxyprogesterone acetate is generally not available without a prescription. With a prescription it is available in three forms:
1. Oral supplement (pills)
2. Aqueous solution for intramuscular injection
3. Aqueous solution for subcutaneous injection

Uses

Medroxyprogesterone acetate is used as a female contraceptive, as part of hormone replacement therapy (HRT) for menopausal symptoms, as a treatment for endometriosis, and for treatment of abnormal sexuality in males.

References

https://en.wikipedia.org/wiki/Medroxyprogesterone_acetate
http://www.chemspider.com/Chemical-Structure.6043.html
https://www.plannedparenthood.org/learn/birth-control/birth-control-pill
https://www.google.com/patents/US3520879

* [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
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